DE2559717A1 - METAL COMPOUNDS AND THEIR USES TO TREAT METAL DEFECTS - Google Patents

METAL COMPOUNDS AND THEIR USES TO TREAT METAL DEFECTS

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Publication number
DE2559717A1
DE2559717A1 DE19752559717 DE2559717A DE2559717A1 DE 2559717 A1 DE2559717 A1 DE 2559717A1 DE 19752559717 DE19752559717 DE 19752559717 DE 2559717 A DE2559717 A DE 2559717A DE 2559717 A1 DE2559717 A1 DE 2559717A1
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Germany
Prior art keywords
coo
metal
chr
molecular weight
amino acids
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
DE19752559717
Other languages
German (de)
Other versions
DE2559717C2 (en
Inventor
Jean-Valentin Morelle
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MORELLE
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MORELLE
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Publication of DE2559717A1 publication Critical patent/DE2559717A1/en
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Publication of DE2559717C2 publication Critical patent/DE2559717C2/de
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Description

DR. KURT JACOBSOHN -> D-8042OBERSCHLEISSHEIM DR. KURT JACOBSOHN -> D-8042OBERSCHLEISSHEIM

PATENTANWALT Freisinger Straße 29 · Postfach / P.O.B. 58PATENT ADVERTISER Freisinger Strasse 29Postfach / P.O.B. 58

29. März 1977March 29, 1977

3 QM3 sqm

Jean-Valentin MORELLEJean-Valentin MORELLE

und
Eliane LAUZANNE-MORELLEand
Eliane LAUZANNE-MORELLE

Paris, FrankreichParis, France

Metallverbindungen und ihre Verwendung zum Behandeln von MetallmangelerscheinungenMetal compounds and their use to treat metal deficiencies

( Ausgeschieden aus der Patentanmeldung P 25 45 194»9-42(Eliminated from patent application P 25 45 194 »9-42

Für diese Anmeldung wird die Priorität vom 28. Oktober 1974 aus der französischen Patentanmeldung Nr. 74.35929 in AnspruchThe priority of October 28, 1974 from French patent application No. 74.35929 is claimed for this application

genommen.taken.

709832/0Q38709832 / 0Q38

Die Erfindung betrifft neue Metallverbindungen, die von besonderem Wert für die Behandlung von Menschen, Tieren und Pflanzen sind.The invention relates to new metal compounds which are of particular value for the treatment of humans, animals and Plants are.

Es ist bekannt, dass bestimmte Mengen von Metallen in allen lebenden Organismen (Menschen, Tieren und Pflanzen) vorkommen und in allen Fällen unentbehrliche Elemente darstellen. Die Metalle kommen im allgemeinen in Form von Proteidkomplexen (Metallproteinen), Glucidoproteidkomplexen oder Lipidoproteidkomplexen vor.It is known that certain amounts of metals are found in all living organisms (humans, animals and plants) and represent indispensable elements in all cases. The metals generally come in the form of protein complexes (Metal proteins), glucidoprotein complexes or lipidoprotein complexes.

Diese Metallverbindungen spielen eine besondere Rolle, die mit der Art des Metalls und der Struktur des komplexbildenden Moleküls selbst variiert; ihre Wirkung liegt auf dem Gebiet der Biokatalyse oder des Stoffwechselaustauschs, auf denen das Überleben oder das Wachstum der Organe oder der Organismen beruht.These metal compounds play a special role, with the type of metal and the structure of the complex-forming Molecule itself varies; their effect is in the field of biocatalysis or metabolic exchange which the survival or growth of organs or organisms is based.

709832/0 008709832/0 008

Das Hauptproblem liegt in der richtigen Auswahl der komplexbildenden Strukturen, die eine solche Beschaffenheit haben müssen, dass sie von dem betreffenden Organ oder Organismus assimiliert oder absorbiert werden.The main problem lies in the correct selection of the complex-forming ones Structures that must be of such a nature that they can be used by the organ or organism in question be assimilated or absorbed.

Lipoaminosäuren und Lipopolyaminosäuren können bekanntlich leicht durch Gewebe und Zellmembranen hindurchdringen, was auf ihren speziellen Lipoproteidstrukturen beruht, die mit den Geweben vollständig verträglich sind. Obwohl die Lipoaminosäuren und Lipopolyaminosäuren wasserunlöslich sind, haben sie ein gewisses Ionisationsvermögen, das auf die in α-Stellung zur Aminogruppe stehende Carboxylgruppe zurückgeht. Die gleichen Eigenschaften haben auch die wasserunlöslichen Salze der Lipoaminosäuren, die ausserdem das jeweilige Metall enthalten.Lipoamino acids and lipopolyamino acids are known to be able to easily penetrate tissue and cell membranes, which is based on their special lipoprotein structures, which are completely compatible with the tissues. Although the lipoamino acids and lipopolyamino acids are water-insoluble, they have a certain ionization capacity, which is due to the in α-position to the amino group decreases carboxyl group. The same properties also have the water-insoluble salts of the lipoamino acids, which also the respective metal contain.

Gegenstand der Erfindung sind neue Verbindungen der allgemeinen FormelThe invention relates to new compounds of the general formula

R-CO- (-NH - CH - Rh (°H)n / M R-CO- (-NH - CH - Rh (° H ) n / M

COO - ICOO - I

lm"n l m " n

in derin the

R-CO den Acylrest einer geradkettigen Fettsäure RCOOH mit 6 bis 20 Kohlenstoffatomen bedeutet,R-CO denotes the acyl radical of a straight-chain fatty acid RCOOH with 6 to 20 carbon atoms,

NH-CH- R1
ι 'NH-CH- R 1
ι '

COO- COOHCOO- COOH

entweder das Gerüst der Aminosäure R^CH-.either the skeleton of the amino acid R ^ CH-.

NH2 ,NH 2 ,

worin R1 die allgemeine Bezeichnung für den Rest irgendeiner der in der Natur vorkommenden Aminosäuren ist, die durch Abbau verschiedener Proteine erhalten werden,where R 1 is the general name for the remainder of any of the naturally occurring amino acids obtained by breaking down various proteins,

oder die Gesamtheit der Gerüste aller ot-Aminosäuren bedeutet, die durch vollständige Hydrolyse von na-or the entirety of the backbones of all ot-amino acids means that by complete hydrolysis of na-

- 2 709832/0988 - 2 709832/0988

türlichen Proteinen erhalten werden, wobei die α-Aminosäuren in ähnlichen Mengenverhältnissen vorliegen wie in den Proteinen, aus denen sie gewonnen worden sind, währendnatural proteins can be obtained, the α-amino acids being present in similar proportions as in the proteins from which they have been obtained while

M Magnesium, Eisen, Kobalt, Mangan, Kupfer oder Zink, m die Wertigkeit des Metalls M undM magnesium, iron, cobalt, manganese, copper or zinc, m the valence of the metal M and

η eine ganze Zahl bedeutet, die kleiner als m ist, oder den Wert Null hat.η means an integer that is smaller than m or has the value zero.

Die oben genannten Metalle sind besonders ausgewählt, da sie normale Bestandteile des menschlichen, tierischen oder pflanzlichen Gewebes und gegenüber diesem Gewebe nicht toxisch sind. Zink soll nur in Präparaten für die Behandlung von Pflanzen verwendet werden, während alle anderen Metalle sich für Mittel zur Behandlung von menschlichem und tierischem Gewebe eignen.The above metals are specially selected as they are normal constituents of human, animal or animal vegetable tissue and are not toxic to this tissue. Zinc is only supposed to be used in preparations for the treatment of Plants are used while all other metals are used for means of treating human and animal tissues suitable.

Die Erfindung stellt z.B. therapeutische Mittel für Menschen und Tiere zur Behebung von Mangelerscheinungen an einigen der oben angegebenen Metalle (vorzugsweise in Form von Cremes, Salben und Gelatinekapseln) sowie Mittel zur Behandlung von Pflanzen zur Verfugung, die die Form wässriger Emulsionen haben können.For example, the invention provides therapeutic agents for humans and animals for remedying deficiencies in some of the metals specified above (preferably in the form of creams, ointments and gelatin capsules) and agents for treatment of plants available, which may be in the form of aqueous emulsions.

Einige Beispiele für derartige Mittel sind die folgenden:Some examples of such agents are the following:

I. Cremes für die lokale Anwendung GewichtsteileI. Creams for topical use parts by weight

A) Magnesiumpalmitoylkollagenat , 5 Polyäthylen-cetylalkohol 5 Glycerin 5 Stearin 7 Isopropylpalmitat 10 Konservierungsmittel nach Bedarf Mit Wasser aufgefüllt auf 100A) magnesium palmitoyl collagenate, 5 Polyethylene cetyl alcohol 5 glycerin 5 stearin 7 isopropyl palmitate 10 Preservatives as required Make up to 100 with water

B) Magnesiumcaprylylglycinat 5 Polyäthylen-cetylalkohol 5 Glycerin 5 Stearin 7B) Magnesium caprylyl glycinate 5 Polyethylene cetyl alcohol 5 glycerin 5 stearin 7

. 3 7 0 9832/0988. 3 7 0 9832/0988

J-J-

Isopropylpalmitat Konservierungsmittel Mit Wasser aufgefüllt aufIsopropyl palmitate preservative Make up with water

GewichtsteileParts by weight

II. Präparate für die orale Darreichung II. Preparations for oral administration

A) Eisenpalmitoylkollagenat LactoseA) Iron palmitoyl collagenate lactose

(für eine Gelatinekapsel von 0,3 g)(for a gelatin capsule of 0.3 g)

B) Manganpalmitoylglycinat LactoseB) Manganese Palmitoyl Glycinate Lactose

(für eine Gelatinekapsel von 0,3 g)(for a gelatin capsule of 0.3 g)

C) Kobaltpalmitoylmethionat LactoseC) Cobalt Palmitoyl Methionate Lactose

(für eine Gelatinekapsel von 0,3 g)(for a gelatin capsule of 0.3 g)

III. Zur Verwendung in der Landwirtschaft III. For use in agriculture

Kupfercaprylylmethionat Polyoxyäthylen-cetylalkohol Mit Wasser aufgefüllt aufCopper caprylyl methionate polyoxyethylene cetyl alcohol Topped up with water

1010 gG gG nach Bedarfupon need gG 100100 gG 0,2500.250 gG 0,0500.050 gG 0,2500.250 GewichtsteileParts by weight 0,0500.050 0,2500.250 0,0500.050

10
10010
100

Diese Metallkomplexverbindungen können entweder durch doppelte Umsetzung zwischen ihren löslichen Salzen (Alkalisalzen) und den entsprechenden löslichen Metallsalzen oder durch Neutralisation der freien Carboxylgruppe mit einer Base oder einem Metalloxidhydrat hergestellt werden. Diese an sich bekannten Reaktionen, die hier nicht näher beschrieben zu werden brauchen, führen zur Bildung von wasserunlöslichen Substanzen, die nach dem Ausfällen, Filtrieren, Waschen und Trocknen Produkte liefern, deren Eigenschaften in der nachstehenden Übersicht angegeben sind, die nach Metallen eingeteilt ist.These metal complex compounds can either be obtained by double conversion between their soluble salts (alkali salts) and the corresponding soluble metal salts or by neutralizing the free carboxyl group with a base or a Metal oxide hydrate can be produced. These reactions, which are known per se and need not be described in more detail here, lead to the formation of water-insoluble substances, which after precipitation, filtration, washing and drying are products whose properties are given in the overview below, which is classified according to metals.

A. Kobaltsalze A. Cobalt Salts

Nr. 1: PalmitoylkollagenatNo. 1: Palmitoyl collagenate

[CH3-(CH2)^-CO-(NH-CHR1)I2 Co Molekular-[CH 3 - (CH 2 ) ^ - CO- (NH-CHR 1 ) I 2 Co Molecular

COO-COO-

gewicht 777weight 777

In der obigen allgemeinen Formel bezeichnetDenoted in the general formula above

709832/0 r. 38709832/0 r . 38

-(NH-CHR1) die Gerüste der Gesamtheit der durch- (NH-CHR 1 ) the scaffolding of the whole of the through

COO-Hydrolyse von Kollagen erhaltenen Aminosäuren.COO hydrolysis of amino acids obtained from collagen.

Nr. 2: PalmitoylmethionatNo. 2: Palmitoyl methionate

S3-S-CH2-CH2 - CH-COO ? lullr- S 3 -S-CH 2 -CH 2 - CH-COO? lullr-

NH-CO-(CH0)-/-CH,C Co gewicht ί 1^ 5J 2 833NH-CO- (CH 0 ) - / - CH, C Co weight ί 1 ^ 5 J 2 833

Nr, 3: CaprylylcystinatNo. 3: caprylyl cystinate

■-OOC-CH-CH^-S - S-CHp-CH-COO-NH NH■ -OOC-CH-CH ^ -S - S-CHp-CH-COO-NH NH

)6-CH3 CO-(CHg)6-CH3 ) 6 -CH 3 CO- (CHg) 6 -CH 3

CO-CO-

CoCo

Molekular gewicht 551Molecular weight 551

Nr. 4.: UndecylenoylglycinatNo. 4: Undecylenoyl Glycinate

[CH2-CH-(CH2)8-C0-NH-CH2-C002] Co[CH 2 -CH- (CH 2 ) 8 -C0 -NH-CH 2 -C00 2 ] Co

Nrο 5: LauroylglycinatNo. 5: Lauroyl glycinate

[CH3-(CHg)6-CO-NH-CH2-COO]2 Co Molekulargewicht 539[CH 3 - (CHg) 6 -CO-NH-CH 2 -COO] 2 Co molecular weight 539

l^To ~l ρ* leu "I η τ*— gewicht 571l ^ To ~ l ρ * leu "I η τ * - weight 571

A = Theoretischer Prozentgehalt B ss Gefundener Prozent gehaltA = Theoretical percentage B ss Percentage found

F. = Schmelzpunkt, °cF. = melting point, ° c

Verbin
dung
Nr.Connect
manure
No.

% Metall % Metal

F.F.

% Stickstoff bez.auf Lipo- bez. auf % Nitrogen based on lipo based on

aminosäure A I B Salz amino acid A I B salt

A j BA j B

AussehenAppearance

11 7,67.6 8,28.2 10L>10L> 22 7,17.1 7, η7, η 33 10,710.7 11,b11, b ;'.Λ0; '. Λ0 44th 10,910.9 9,29.2 160160 55 10,310.3 9,39.3 145145

3.9 5,63.9 5.6

5.4 4,0 3, 5.4 4.0 3,

1^,1 '«,'i 1 ^, 1 '«,' i

5,5,

4,4 4,14.4 4.1

V ίο I «· U,-V ίο I «· U, -

709832/0888709832/0888

B. Kupfersalze B. Copper Salts

Nr. 6: Caprylylglycinat [CH3-(CH2)6-CO-NK-CK2-COO]2 CuNo. 6: Caprylyl glycinate [CH 3 - (CH 2 ) 6-CO-NK-CK 2 -COO] 2 Cu

Nr. 7: CaprylylmethionatNo. 7: caprylyl methionate

CH3-S-CH2-CH2-CH-COO-CH 3 -S-CH 2 -CH 2 -CH-COO-

NH-OC-(CH0)NH-OC- (CH 0 )

Nr. 8: Pulmitoylkolla^onaLNo. 8: Pulmitoylkolla ^ onaL

2)6-CH3J 2 ) 6 -CH 3 J

CuCu

NH-CHR1 COO-NH-CHR 1 COO-

CuCu

Für aie Bedeutung des Restes -(Mi-CHR1) vgl. Verbindung Nr. 1 COO-For the meaning of the remainder - (Mi-CHR 1 ) see Compound No. 1 COO-

Nr. 9ϊ PalrnitoylkeratinatNo. 9ϊ palnitoyl keratinate

CH3-(CH2)14-(XK NH-CHR1)CH 3 - (CH 2 ) 14 - (XK NH-CHR 1 )

COO-COO-

Für die Definition vgl. Verbindung Nr. 20 mit dem Unterschied, dass Kollagen durch Keratin ersetzt wird.For the definition see connection no. 20 with the difference, that collagen is replaced by keratin.

Nr. 10: CaprylylkollagenatNo. 10: caprylyl collagenate

CH3- ( CH2 ) 6-C0- ( NH-CHR1)CH 3 - (CH 2 ) 6 -C0- (NH-CHR 1 )

COO-COO-

CuCu

Definition vgl. Verbindung Nr. 8For definition see connection no.8

Molekulargewicht Molecular weight

Molekulargewicht 611Molecular weight 611

Molukuiax·- gewicht 7b1Molukuiax · - weight 7b1

Molekulargewicht 821Molecular weight 821

Molekulargewicht 555Molecular weight 555

709832/0988709832/0988

Nr. 11: LauroylkollagenatNo. 11: Lauroyl collagenate

Q-CO-(NH-CHR1 ) Q-CO- (NH-CHR 1 )

COQ-COQ-

CuCu

Molekulargewicht Molecular weight

.Definition vgl. Verbindung Nr. 8 Nr. 12: Oleylkollagenat.Definition see Compound No. 8 No. 12: Oleyl Collagenate

[CH3-(CH2J7-CHaCH-(CH2J7-CO-(NH-CHR1 j] Cu COO-J2 [CH 3 - (CH 2 J 7 -CHaCH- (CH 2 J 7 -CO- (NH-CHR 1 j] Cu COO-J 2

De Π nit ion vgl. Verbindung Nr. 8 De Π nit ion see compound no.8

MoIu-MoIu-

gewicht 829weight 829

A « Theoretischer Prozentgehalt B β Gefundener Prozentgehalt A « Theoretical percentage B β Percentage found

F. «a Schmelzpunkt, CF. «a melting point, C.

Verbin dungLink

% Metall % Metal

% Stickstoff bez.auf Lipo- bez. auf. % Nitrogen based on lipo based on.

aminosäure AjB amino acid AjB

Salz
A I Bsalt
AIB

AussehenAppearance

66th 13,Ji13, Ji 11, H11, H. ensalzeossalts 17u17u !',1!',1 V/V / C)C) 22 ',', ,7, 7 77th 10,510.5 υ, 7υ, 7 1HO1HO ''.77 V'V ' /.,r,/.,r, 55 88th 0,10.1 7,57.5 H',H', 3,73.7 3,43.4 VV 44th ,;,; 99 7,77.7 6,96.9 HOHO 5,75.7 5,45.4 3,43.4 33 ,1,1 1010 11,411.4 9,89.8 145145 4,64.6 4,34.3 5,05.0 22 ,7, 7 1111 9,59.5 8,68.6 9090 8,18.1 7,47.4 4,24.2 ,8,8th 1212th 7,67.6 6,96.9 5555 3,13.1 ,8,8th C. Eis C. Ice 13: Palmitoylkollagenat13: Palmitoyl collagenate Nr.No. -CO-(NH-CHR1 ) -CO- (NH-CHR 1 ) PePe CH3-(CH2)14 CH 3 - (CH 2 ) 14 coo-_coo-_

Pulverpowder

Molekulargewicht 774Molecular weight 774

Für die Bedeutung des Restes
-(NH-CHR1) vgl. Verbindung Nr. 1For the importance of the rest
- (NH-CHR 1 ) see Compound No. 1

COO-COO-

- 7 709832/0988 - 7 709832/0988

Nr. 14: CaprylylkollagenatNo. 14: Caprylyl collagenate

CH3-(CH2J6-CO-(NH-CHR1 CH 3 - (CH 2 J 6 -CO- (NH-CHR 1

COO-COO-

FeFe

Definition vgl. Verbindung Nr. 13For definition see connection no.13

D. Zinksalze D. zinc salts

Nr. 15: CaprylylglycinatNo. 15: Caprylyl Glycinate

CH3-(CH2)6-CO-(NH-CHR1 CH 3 - (CH 2 ) 6 -CO- (NH-CHR 1

-CHR1 ). COO-_[-CHR 1 ). COO -_ [

Für die Bedeutung des Restes -(NH-CHR1) vgl. Verbindung Nr. 1 COO-For the meaning of the remainder - (NH-CHR 1 ) cf.compound no. 1 COO-

E. Mangansalze E. Manganese salts

Nr. 16: PalmxtoylkollagenatNo. 16: palm xtoyl collagenate

CH3-(CH2)14-C0-(NH-CHR1 CH 3 - (CH 2 ) 14 -C0- (NH-CHR 1

COO-COO-

MnMn

Für die Bedeutung des Restes -(NH-CHR1) vgl. Verbindung Nr. 1 COO-For the meaning of the remainder - (NH-CHR 1 ) cf.compound no. 1 COO-

Nr. 17: CaprylylglycinatNo. 17: Caprylyl Glycinate

Urin— ι w»n — J /-—ου— ^iMnj do Urine— ι w »n - J / -— ου— ^ iMnj do

COO-COO-

Definition vgl. Verbindung Nr. 16For definition see connection no.16

Molekulargewicht 550Molecular weight 550

Molekulargewicht 465Molecular weight 465

Molekulargewicht 773Molecular weight 773

Molekulargewicht 455Molecular weight 455

709832/0^88709832/0 ^ 88

A
B A.
B. « Theoretischer Prozent gehalt
a Gefundener Prozentgehalt « Theoretical percentage
a Percentage found F.F. bez.c
amine
A re c
amine
A. % Stick«
mf Lipo-
) säure
B % Stick «
mf lipo-
) acid
B. F, « Schmelzpunkt, 0C F, « melting point, 0 C AussehenAppearance Ver
bin
dung
Nr. Ver
am
manure
No. % % Me 1Me 1
AA. >200> 200 7,07.0 v»v » stoff
bez. auf
Sals
A } B material
related to
Sals
A } B ro l;-()(;ki'i1-
Γ; ι rl mn nt;
I'υ l v.T
WC" i f.!Iiι.'U
Pulver ro l; - () (; ki'i 1 -
Γ; ι rl mn nt;
I'υ l vT
WC "i f.! Iiι.'U
powder 13
1413th
14th 10,1
13,9 '10.1
13.9 ' 0,0 lj, 10.0 l j, 1 :all
B :Alles
B.

7,1 6,7 97 3,9 3,6 3,6 3,2 ) gelbgraues7.1 6.7 97 3.9 3.6 3.6 3.2) yellow-gray

12 13,2 199 6,9 6,8 6,1 5,8 J Pulver12 13.2 199 6.9 6.8 6.1 5.8 J powder

F. Magnesiumsalze F. Magnesium salts

Nr. 18: PalmitoylkollagenatNo. 18: Palmitoyl collagenate

CH3-(CH2)14-C0-(NH-CHR1'TCH 3 - (CH 2 ) 14 -C0- (NH-CHR 1 'T

COO-COO-

Molekulargewicht 742Molecular weight 742

Für die Bedeutung des Restes -(NH-CIiR1) vgl. Verbindung Nr. COO-For the meaning of the remainder - (NH-CIiR 1 ) cf.compound no. COO-

Nr. 19: CaprylylkollagenatNo. 19: Caprylyl collagenate

(CH2J6-(CH 2 J 6 -

COO-COO-

MgMg

Molekulargewicht 518Molecular weight 518

Definition vgl. Verbindung Nr. Nr. 20: Pnlmitoy"l.ni(! thJ on.'itDefinition see connection no. No. 20: Pnlmitoy "l.ni (! ThJ on.'it

CH3-S-CH2-CH2-CH-CuO-CH 3 -S-CH 2 -CH 2 -CH-CuO-

NHNH

:-co-(ch2)14-ch3 : -co- (ch 2 ) 14 -ch 3

MgMg

_ 2_ 2

Fl i) I ι · -Fl i) I ι -

ku I · ι C-guwicht 796 ku I · ι C- guwicht 796

709832/09B8709832 / 09B8

-73-73

Nr. 21: CaprylylmethionatNo. 21: caprylyl methionate

CH3-S-CH2-CH2-CH-COO-NH-C0- CH 3 -S-CH 2 -CH 2 -CH-COO-NH-C0-

£J 2£ J 2

Nr. 22: CaprylylgiycinatNo. 22: Caprylyl giycinate

[CH3-(CH2)6-C0-NH-CH2-C00]2 Mg[CH 3 - (CH 2 ) 6 -C0-NH-CH 2 -C00] 2 Mg

Nr. 23: LauroylasparaginatNo. 23: Lauroylaspartate

Q-CO-NH-CH-CH2COO-COO- Q-CO-NH-CH-CH 2 COO-COO-

MgMg

Nr. 24: CaproylglycinatNo. 24: Caproyl Glycinate

-(CH2 J4-CO-NH-CIl2-COO] 2 Mg- (CH 2 J 4 -CO-NH-Cl 2 -COO] 2 Mg

Molekulargewicht 572Molecular weight 572

Molekulargewicht 424Molecular weight 424

Molekulargewicht 337Molecular weight 337

Molekulargewicht 368Molecular weight 368

Λ ·" Thnori'LL'tchujc l'roiumt »joint L L Ii ■ Gefundener Prozent gehaltΛ · "Thnori'LL'tchujc l'roiumt» joint L L Ii ■ Percentage found

I''. -« iichmulifipunkL, (jI ''. - «iichmulifipunkL, (j

Verbin
dung
Nr.Connect
manure
No.

% % Metallmetal

P.P.

% Stickstoff beζ»auf Lipo- bez. auf % Nitrogen based on lipo

aminosäure A I Bamino acid A I B

Salz AjBsalt AjB

AussehenAppearance

1818th VV k,2.k, 2. 9999 3,93.9 vv 5,H5, H. 3,43.4 1919th /i,r./ i, r. 2,72.7 IU'iIU'i 5,45.4 2O2O 3,o3, o 3,83.8 ISYISY V·V 4,74.7 2121 4,24.2 5,25.2 200200 5,15.1 6,86.8 4,94.9 4,7 <4.7 < 2222nd 5,65.6 7,87.8 185185 6,96.9 4,14.1 6,66.6 6,2 ;6.2; 2323 7,17.1 5,95.9 >200> 200 4,44.4 7,47.4 4,14.1 3,8 .3.8. 2424 6,56.5 >200> 200 8,18.1 7,67.6 7,17.1

Pulverpowder

Die Verbindungen gemäss der Erfindung können z.B. für die folgenden Zwecke verwendet werden:The compounds according to the invention can e.g. can be used for the following purposes:

- 10 -- 10 -

709832/0988709832/0988

üiu iVüoaltsalze als blutbildende Mittel;üiu iVüoaltsalze as hematopoietic agents;

uifi ftangan- una Magnesiumsalze als Wuchsmittel, besonders für Vieh;uifi ftangan- una magnesium salts as growth agents, especially for Cattle;

uie Kupfersaizti als bioaynthetische Stoffe (Synthese von Cuproproteinen) und zur Behandlung von Kryptogamenerkrankun-uie Kupfersaizti as bio-aesthetic substances (synthesis of Cuproproteins) and for the treatment of cryptogamous diseases

rinde der Beschreibung.bark of description.

709832/0988709832/0988

Claims (1)

PatentansprücheClaims entweder das Gerüst der Aminosäureeither the backbone of the amino acid in der R^ die allgemeine Bezeichnung für den Rest irgendeiner der in der Natur vorkommenden Aminosäuren ist, die durch Abbau verschiedener Proteine erhalten werden,in the R ^ the general name for the rest any of the naturally occurring amino acids is produced by the breakdown of various proteins be obtained oder die Gesamtheit der Gerüste aller cc-Amino säuren bedeutet, die durch vollständige Hydrolyse von natürlichen Proteinen erhalten werden, wobei die α-Aminosäuren in ähnlichen Mengenverhältnissen vorliegen .wie in den Proteinen, aus denen sie gewonnen worden sind, währendor the totality of the skeletons of all cc-amino acids means obtained by complete hydrolysis of natural proteins, the α-Amino acids are present in similar proportions as in the proteins from which they are obtained have been while 709832/0988709832/0988 255971?255971? M Magnesium, Eisen, Kobalt, Mangan, Kupfer oder Zink,M magnesium, iron, cobalt, manganese, copper or zinc, m die Wertigkeit des Metalls M undm the valence of the metal M and η eine ganze Zahl bedeutet, die kleiner als m ist.η means an integer smaller than m. 2o Mittel zum Behandeln von Metallmangelerscheinungen bei Menschen, Tieren und Pflanzen, dadurch gekennzeichnet, dass es als Wirkstoff mindestens eine Verbindung gemäss Anspruch 1 enthältο2o agents for treating metal deficiency symptoms Humans, animals and plants, characterized in that there is at least one compound according to claim as active ingredient 1 contains o 709832/0988709832/0988
DE19752559717 1974-10-28 1975-10-09 METAL COMPOUNDS AND THEIR USES TO TREAT METAL DEFECTS Granted DE2559717A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7435929A FR2289179A1 (en) 1974-10-28 1974-10-28 METAL SALTS OF LIPOAMINOACIDS

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DE2559717A1 true DE2559717A1 (en) 1977-08-11
DE2559717C2 DE2559717C2 (en) 1988-03-03

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DE2545194A Expired DE2545194C2 (en) 1974-10-28 1975-10-09 Agent for the treatment of hyperhidrosis for topical use
DE19752559717 Granted DE2559717A1 (en) 1974-10-28 1975-10-09 METAL COMPOUNDS AND THEIR USES TO TREAT METAL DEFECTS

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DE2545194A Expired DE2545194C2 (en) 1974-10-28 1975-10-09 Agent for the treatment of hyperhidrosis for topical use

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DE (2) DE2545194C2 (en)
FR (1) FR2289179A1 (en)
GB (1) GB1468646A (en)

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JPS55118971A (en) * 1979-03-08 1980-09-12 Nippon Shikizai Kogyo Kenkyusho:Kk Brightness modifier and modification of brightness
FR2462192B1 (en) * 1979-08-02 1986-08-01 Oreal "WATER-IN-OIL" TYPE EMULSIONS FOR USE AS COSMETIC SUPPORTS OR PHARMACEUTICAL EXCIPIENTS
JPS58140026A (en) * 1982-01-14 1983-08-19 Toyo Jozo Co Ltd Pharmaceutical having improved absorbability
FR2503153A1 (en) * 1981-04-02 1982-10-08 Morelle Jean Compsns. contg. N-butyryl alpha-aminoacid(s) - for cosmetic, hygienic, therapeutic or agricultural use
JPS5872512A (en) * 1981-10-26 1983-04-30 Miyoshi Kasei:Kk Make-up cosmetic
US4675422A (en) * 1985-10-23 1987-06-23 Stepan Company Organometallic compounds
FR2636238B1 (en) * 1988-09-14 1994-01-21 Morelle Jean NEW ANTISUDORAL COMPOSITIONS
FR2649697A1 (en) * 1989-07-11 1991-01-18 Oreal NOVEL URETHANNE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN PARTICULAR AS MOISTURIZING AGENTS IN COSMETIC OR PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OF DRY SKINS
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US5889050A (en) * 1991-06-21 1999-03-30 Astra Aktiebolag 3,3'-dithiobis (propionic acids) and esters thereof
FR2698869B1 (en) * 1992-12-09 1995-02-24 Morelle Jean Acylamino acids obtained from fibers from Bombyx Mori.
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Also Published As

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DE2545194C2 (en) 1985-06-20
FR2289179A1 (en) 1976-05-28
GB1468646A (en) 1977-03-30
US4089954A (en) 1978-05-16
DE2545194A1 (en) 1976-04-29
FR2289179B1 (en) 1978-07-21
DE2559717C2 (en) 1988-03-03

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